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Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Nomenclature of Carboxylic Acid Derivatives: Amides and Nitriles

Naming Amides
The IUPAC and common names of amides are derived from the parent carboxylic acid, by replacing the suffix “oic acid” and “ic acid,” respectively, with “amide.” In the following example, the IUPAC name ethanamide is derived from ethanoic acid, and the common name, acetamide, is obtained from acetic acid.

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.

Diazonium Group Substitution: –OH and –H

Diazonium Group Substitution: –OH and –H

Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.

Amines to Amides: Acylation of Amines

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...

Structures of Carboxylic Acid Derivatives

Structures of Carboxylic Acid Derivatives

Structure of Carboxylic Acid Derivatives
Carboxylic acid derivatives contain an acyl group attached to a heteroatom such as chlorine, oxygen, or nitrogen. The carbonyl carbon and oxygen are both sp2-hybridized with an unhybridized p orbital.
The three sp2 orbitals of the carbonyl carbon form three σ bonds, one each with the carbonyl oxygen, the α carbon, and the heteroatom, whereas the other two sp2 orbitals of the carbonyl oxygen are occupied by the lone pairs. Further, the unhybridized p...

Preparation of Amides

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...

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Updated: Jun 1, 2026

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Preparation and In Vivo Use of an Activity-based Probe for N-acylethanolamine Acid Amidase

Published on: November 23, 2016

2,2-Dichloro-N-(3,4-dimethyl-phen-yl)acetamide.

B Thimme Gowda, Sabine Foro, Ingrid Svoboda

Acta Crystallographica. Section E, Structure Reports Online

|May 18, 2011

Summary

This study details the molecular structure of a dichloro-acetamide compound. It highlights the syn conformation of the N-H bond relative to the aromatic methyl group and its anti conformation to the carbonyl group, forming hydrogen-bonded chains.

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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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Published on: April 27, 2017

Area of Science:

Crystallography
Organic Chemistry
Molecular Structure Analysis

Background:

Understanding the conformational preferences of N-substituted acetamides is crucial for predicting their chemical behavior and intermolecular interactions.
Previous studies have established specific conformational relationships between substituents on aromatic rings and amide groups in related compounds.

Purpose of the Study:

To elucidate the precise molecular conformation and intermolecular interactions of the title compound, C(10)H(11)Cl(2)NO.
To compare the observed conformation with related dichloro-acetamide derivatives and analyze the influence of substituents.

Main Methods:

Single-crystal X-ray diffraction was employed to determine the three-dimensional molecular structure.
Analysis of bond lengths, bond angles, and torsion angles characterized the molecular geometry.
Identification and analysis of intermolecular hydrogen bonding networks.

Main Results:

The N-H bond was found to be in a syn conformation relative to the 3-methyl substituent on the aromatic ring.
The N-H bond adopted an anti conformation with respect to the carbonyl (C=O) bond.
An intermolecular N-H⋯O hydrogen bond was identified, leading to the formation of infinite molecular chains along the b-axis.

Conclusions:

The study confirms specific conformational preferences in dichloro-acetamide derivatives, influenced by aromatic ring substituents.
The observed hydrogen bonding pattern dictates the crystal packing and solid-state structure.
This detailed structural analysis provides valuable data for structure-activity relationship studies in related chemical series.